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140-Mile Tuscan Road Trip Explores Piero della Francesca’s Art

Covering roughly 140 miles for roughly $450 per person, art enthusiasts embarking on a 140-mile Tuscan road trip departing Florence at 8:30 a.m.

140-Mile Tuscan Road Trip Explores Piero della Francesca's Art
140-Mile Tuscan Road Trip Explores Piero della Francesca's Art

Covering roughly 140 miles for roughly $450 per person, art enthusiasts embarking on a 140-mile Tuscan road trip departing Florence at 8:30 a.m. can explore major works by Renaissance master Piero della Francesca in Sansepolcro, Monterchi, and Arezzo.

For travelers willing to venture beyond Florence—where Piero is represented only by small portraits of the Duke and Duchess of Urbino at the Uffizi Gallery—eastern Tuscany offers a concentrated look at the 15th-century master’s monumental works. A group of four travelers sharing the cost of a car, driver, and guide set out on an all-day excursion covering roughly 140 miles, designed to trace the artist’s roots and masterpieces across Sansepolcro, Monterchi, and Arezzo.

The Resurrection Fresco Survives Centuries of Damage

Painted around seven feet on each side, the imposing fresco The Resurrection portrays Christ rising three days after crucifixion and entombment. The artwork survived being plastered over in 1463, a rediscovery process that took centuries, and later escaped demolition during World War II.

The composition features an idealized muscular Christ stepping out of a carved stone tomb while holding a banner, accompanied by sleeping soldiers in the foreground—one of whom, dressed in brown, is said to be a self-portrait. The Museo Civico also houses two small fresco portraits of Saints Louis of Toulouse and Julian by Piero, alongside the gilded and dramatically lit Polyptych of the Misericordia.

Madonna Del Parto Honors the Artist's Mother

Art enthusiasts leaving Sansepolcro at 11:30 a.m. drove about 30 minutes to the crenelated hilltop village of Monterchi. Before visiting the local Museo Civico to view the Madonna del Parto, the group stopped for lunch at La Terrazza di Piero, a small rustic restaurant offering one of roughly three dining options in the village.

Supposedly painted between 1455 and 1465 for the Cappella di Santa Maria di Momentana, the fresco honors the artist’s mother, Romana di Pierino da Monterchi, who was born in the village. Over the centuries, the artwork has became a destination for women seeking protection during pregnancy or hoping to bear a child. The arresting painting depicts a visibly pregnant Madonna opening her blue dress slightly at the waist, flanked by a pair of angels parting a tent embroidered with pomegranates, a recognized symbol of fertility.

Art Enthusiasts Return to Florence for Negronis

Art enthusiasts completed the entire loop with a return to Florence at 6:30 p.m. Art enthusiasts departing Florence at 8:30 a.m. finished the journey at Giacosa 1815, a luxurious bar on Via della Spada that claims to have created the Negroni when the establishment was located across the street. There, a flight of Negronis awaited them to cap off the day.

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Culture Editor

Lucia Moretti

Lucia Moretti is the editorial identity for TellingPointy's Culture desk, exploring film, television, music, books, gaming, creators, and the media industries around them. Moretti treats culture as both art and infrastructure: a place where taste, technology, money, identity, and power meet. Her desk moves beyond publicity cycles to ask why a work resonates, how it was made and distributed, whose perspective is missing, and what its reception reveals about the moment.